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356068-86-5

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356068-86-5 Usage

Uses

N-[2-(Diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide is used in the preparation of (pyrrolylmethylidene)indolinones as tyrosine kinase inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 356068-86-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,5,6,0,6 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 356068-86:
(8*3)+(7*5)+(6*6)+(5*0)+(4*6)+(3*8)+(2*8)+(1*6)=165
165 % 10 = 5
So 356068-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H23N3O2/c1-5-17(6-2)8-7-15-14(19)13-10(3)12(9-18)16-11(13)4/h9,16H,5-8H2,1-4H3,(H,15,19)

356068-86-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name N-[2-(diethylamino)ethyl]-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:356068-86-5 SDS

356068-86-5Synthetic route

5-[(2-diethylamino-ethylimino)-methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-[(2-diethylamino-ethylimino)-methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With water100%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 59h;86.3%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide84%
Stage #1: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: N,N-diethylethylenediamine With triethylamine In N,N-dimethyl-formamide at 20℃;
80%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

N,N-diethylhydrazine
616-40-0

N,N-diethylhydrazine

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 59h;86.3%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride

1-(3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene43%
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene43%
With sodium hydroxide; triethylamine In N-methyl-acetamide; methanol; dichloromethane; water; ethyl acetate; toluene43%
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 45 °C
2: imidazole / carbon dioxide / tetrahydrofuran / 45 °C
3: 100 percent / H2O
View Scheme
4-(imidazole-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde
452105-37-2

4-(imidazole-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: imidazole / carbon dioxide / tetrahydrofuran / 45 °C
2: 100 percent / H2O
View Scheme
ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate
2199-59-9

ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / aq. KOH / methanol / 3 h / Heating
2: 50 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
2.2: 16 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: water; potassium hydroxide / methanol / 3 h / Reflux
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C
View Scheme
2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
86770-31-2

2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / TFA / -5 - 20 °C
2: 90 percent / aq. KOH / methanol / 3 h / Heating
3: 50 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / isopropyl alcohol / 25 - 50 °C
2.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
2.2: 25 - 30 °C / pH 12 - 13
3.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
4.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
4.2: 16 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / ethanol / 3 h / 70 °C
2: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux
3: water; potassium hydroxide / methanol / 3 h / Reflux
4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / ethanol; water / 1 h / 60 °C
2: trichlorophosphate / dichloromethane / 2 h / Reflux
3: potassium hydroxide / methanol; water / 4 h / Reflux
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide
View Scheme
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

A

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylarnino-ethyl)-amide

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylarnino-ethyl)-amide

B

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
A 6.19g (78%)
B n/a
2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester
2199-51-1

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
1.2: 25 - 30 °C / pH 12 - 13
2.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
3.2: 16 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / 1,2-dichloro-ethane / 2 h / Reflux
2: water; potassium hydroxide / methanol / 3 h / Reflux
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 12 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux
1.2: 0.5 h / Reflux
2.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere
3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: trichlorophosphate / dichloromethane / 2 h / Reflux
2: potassium hydroxide / methanol; water / 4 h / Reflux
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C
1.2: 1.5 h / Reflux
2.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere
3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate
2436-79-5

diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water; potassium hydroxide / ethanol / 10 h / 50 - 60 °C
2.1: Inert atmosphere
3.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux
3.2: 0.5 h / Reflux
4.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere
5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium hydroxide / ethanol; water / 10 h / 50 °C
2.1: 0.08 h / 200 °C / Inert atmosphere
3.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C
3.2: 1.5 h / Reflux
4.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere
5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-ethyl ester
5442-91-1

3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-ethyl ester

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Inert atmosphere
2.1: trichlorophosphate / dichloromethane / 1.5 h / Reflux
2.2: 0.5 h / Reflux
3.1: sodium hydroxide; water / methanol / 4.5 h / 82 - 83 °C / Inert atmosphere
4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 0.08 h / 200 °C / Inert atmosphere
2.1: trichlorophosphate / dichloromethane / 0.5 h / 0 °C
2.2: 1.5 h / Reflux
3.1: sodium hydroxide / water; methanol / 4.5 h / Reflux; Inert atmosphere
4.1: dicyclohexyl-carbodiimide; dmap / dichloromethane; N,N-dimethyl-formamide / 59 h / 0 - 20 °C
View Scheme
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
590424-05-8

N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With oxalyl dichloride In dichloromethane at 0 - 10℃; for 2.5h; Inert atmosphere;
Stage #2: N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide In dichloromethane at 30℃;
tert-butyl 4-[[[2-(diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate
590424-04-7

tert-butyl 4-[[[2-(diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C
2.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere
2.2: 30 °C
View Scheme
N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dichloromethane / 0.5 h / 0 - 20 °C
2.1: zinc / methanol; acetic acid / 65 - 70 °C
3.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C
4.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere
4.2: 30 °C
View Scheme
N-(2-(diethylamino)ethyl)-3-oxobutanamide
590424-03-6

N-(2-(diethylamino)ethyl)-3-oxobutanamide

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: zinc / methanol; acetic acid / 65 - 70 °C
2.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C
3.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere
3.2: 30 °C
View Scheme
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib
557795-19-4

sunitinib

Conditions
ConditionsYield
With piperidine In toluene for 3h; Solvent; Reagent/catalyst; Knoevenagel Condensation; Reflux;97.3%
With piperidine In toluene for 3h; Reagent/catalyst; Solvent; Reflux;97.3%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3.5h; Aldol Condensation; Darkness; Inert atmosphere;94%
5-bromo-2-indolin-2-one
20870-78-4

5-bromo-2-indolin-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)amide

5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)amide

Conditions
ConditionsYield
With piperidine In ethanol at 90℃; for 6h; Knoevenagel condensation;96%
0.09 g (26%)
0.09 g (26%)
With piperidine In ethanol at 80℃; for 1h;368 mg
C43H37Br2NP2

C43H37Br2NP2

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

C35H51N7O2

C35H51N7O2

Conditions
ConditionsYield
Stage #1: C43H37Br2NP2 With n-butyllithium In tetrahydrofuran at -75℃; for 0.5h;
Stage #2: N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In tetrahydrofuran for 2h;
91%
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide-α-d1

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide-α-d1

Conditions
ConditionsYield
With 1,3-bis-(2,4,6-trimethylphenyl)-4,5-dihydro-3H-imidazol-1-ium bromide; water-d2; potassium carbonate In dichloromethane at 80℃; for 12h;88%
(S)-Malic acid
97-67-6

(S)-Malic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

L-(-)-malic acid of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide
1200435-83-1

L-(-)-malic acid of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide

Conditions
ConditionsYield
In dichloromethane at 25 - 30℃;86%
In butan-1-ol at 57℃;
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(S)-Malic acid
97-67-6

(S)-Malic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib L-malate

sunitinib L-malate

Conditions
ConditionsYield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In ethanol for 1.5h; Reflux;
Stage #2: (S)-Malic acid In ethanol Product distribution / selectivity;
84%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

tert-butyl-3-[(tert-butoxycarbonyl)(2-(diethylamino)ethyl)carbamoyl]-5-formyl-2,4-dimethyl-1H-pyrrole-1-carboxylate

tert-butyl-3-[(tert-butoxycarbonyl)(2-(diethylamino)ethyl)carbamoyl]-5-formyl-2,4-dimethyl-1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
Stage #1: N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With dmap In dichloromethane at 20℃; for 0.166667h;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 50h;
84%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(S)-Malic acid
97-67-6

(S)-Malic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
With pyrrolidine In ethanol at 78℃; for 3h;80%
With pyrrolidine In ethanol at 78℃; for 3h;80%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In butan-1-ol at 48℃;
Stage #2: 5-fluoroindol-2(3H)-one With pyrrolidine In butan-1-ol at 94℃; Product distribution / selectivity;
71.2%
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In ethanol at 8 - 10℃; Reflux;
Stage #2: (S)-Malic acid In ethanol for 4 - 6h; Product distribution / selectivity; Reflux;
71%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In tetrahydrofuran for 4 - 6h;
Stage #2: 5-fluoroindol-2(3H)-one In tetrahydrofuran for 4 - 6h; Product distribution / selectivity; Reflux;
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2-(N,N-diethylamino)ethyl ammonium di(L-malate)

2-(N,N-diethylamino)ethyl ammonium di(L-malate)

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;80%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(S)-Malic acid
97-67-6

(S)-Malic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide L-malate

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide L-malate

Conditions
ConditionsYield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In ethanol at 78℃; for 1.5h;
Stage #2: (S)-Malic acid In ethanol at 78℃; for 1h;
80%
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

C14H24N3O5S(1-)*Na(1+)
1338703-87-9

C14H24N3O5S(1-)*Na(1+)

Conditions
ConditionsYield
With sodium hydrogensulfite In ethanol; water at 10 - 20℃;79%
piperidine
110-89-4

piperidine

4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one
442562-94-9

4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

5-[4-(3-Methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)-amide

5-[4-(3-Methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)-amide

Conditions
ConditionsYield
In ethanol78%
5-hydroxy-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

5-hydroxy-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-N-(2-(diethylamino)ethyl)-5-((5-hydroxy-4,6-dimethyl-2-oxo-1H-pyrrolo[2,3-b]pyridin-3(2H)-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-N-(2-(diethylamino)ethyl)-5-((5-hydroxy-4,6-dimethyl-2-oxo-1H-pyrrolo[2,3-b]pyridin-3(2H)-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With piperidine In ethanol for 20h; Knoevenagel Condensation; Reflux;77%
5-iodo-1,3-dihydro-indol-2-one
193354-13-1

5-iodo-1,3-dihydro-indol-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-iodo-1,2-dihydro-2-oxo-3H-indole-3-ylidine)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
1372783-13-5

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-iodo-1,2-dihydro-2-oxo-3H-indole-3-ylidine)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With piperidine In ethanol at 90℃; for 5h; Knoevenagel condensation;76%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

acetic acid
64-19-7

acetic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib acetate
1221149-36-5

sunitinib acetate

Conditions
ConditionsYield
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With pyrrolidine In butan-1-ol at 20℃; Reflux;
Stage #2: acetic acid In butan-1-ol Reflux;
75.3%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

di-(n-propyl ammonium) L-malate

di-(n-propyl ammonium) L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
6-chloro-2-oxindole
56341-37-8

6-chloro-2-oxindole

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((6-chloro-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((6-chloro-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With pyrrolidine In ethanol for 3h; Reflux;74%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

di-(diisopropyl ammonium) L-malate

di-(diisopropyl ammonium) L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72.5%
piperidine
110-89-4

piperidine

4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one
442562-93-8

4-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

5-[4-(4-methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-[4-(4-methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions
ConditionsYield
In ethanol72%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2-(N,N-diethylamino)ethyl ammonium L-malate
1332307-07-9

2-(N,N-diethylamino)ethyl ammonium L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72%
piperidine
110-89-4

piperidine

4-(4-fluoro-phenyl)-1,3-dihydro-indol-2-one
442562-87-0

4-(4-fluoro-phenyl)-1,3-dihydro-indol-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

5-[4-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-[4-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions
ConditionsYield
In ethanol70%
(S)-Malic acid
97-67-6

(S)-Malic acid

5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole
1374685-40-1

5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux;
Stage #2: (S)-Malic acid In methanol; acetonitrile at 20℃; for 22h;
70%
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux;
Stage #2: (S)-Malic acid In methanol for 24h;
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 9.5h; Reflux;
Stage #2: (S)-Malic acid In methanol for 24h;
5-(2-azidoethyl)indolin-2-one

5-(2-azidoethyl)indolin-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((5-(2-azidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((5-(2-azidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With pyrrolidine In ethanol for 3h; Reflux;68%
piperidine
110-89-4

piperidine

4-(3-bromo-phenyl)-1,3-dihydro-indol-2-one
442562-92-7

4-(3-bromo-phenyl)-1,3-dihydro-indol-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

A

5-l4-(3-Bromophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-l4-(3-Bromophenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

B

5-[4-(3-bromo-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

5-[4-(3-bromo-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide

Conditions
ConditionsYield
In ethanolA 67%
B n/a
5-azaindolin-2-one
134682-54-5

5-azaindolin-2-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-1H-pyrrolo[3,2-c]pyridin-3(2H)-ylidene)methyl)-1H-pyrrole-3-carboxamide
1350702-94-1

(Z)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-5-((2-oxo-1H-pyrrolo[3,2-c]pyridin-3(2H)-ylidene)methyl)-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With piperidine In methanol for 5h; Reflux;62%
N-(2-(2-oxoindolin-5-yl)ethyl)acetamide

N-(2-(2-oxoindolin-5-yl)ethyl)acetamide

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((5-(2-acetamidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

(Z)-5-((5-(2-acetamidoethyl)-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Conditions
ConditionsYield
With pyrrolidine In ethanol for 3h; Reflux;62%

356068-86-5Relevant articles and documents

AMP-ACTIVATED PROTEIN KINASE INHIBITORS AND METHODS OF MAKING AND USING THE SAME

-

Page/Page column 82-83, (2021/01/23)

The present disclosure relates to compounds of Formula (I): (I); stereoisomers thereof, prodrugs thereof, and pharmaceutically acceptable salts thereof. The present disclosure also relates to uses of the compounds, e.g., to inhibit AMP-Activated protein kinase (AMPK) and treat cancer in a subject.

Substituted oxindol-3-ylidenes as AMP-activated protein kinase (AMPK) inhibitors

Backos, Donald S.,Casalvieri, Kimberly A.,Jordan, Craig T.,Matheson, Christopher J.,Minhajuddin, Mohammed,Reigan, Philip

, (2020/04/22)

AMP-activated protein kinase (AMPK) is a central metabolic regulator that promotes cancer growth and survival under hypoxia and plays a role in the maintenance of cancer stem cells. A major challenge to interrogating the potential of targeting AMPK in cancer is the lack of potent and selective small molecule inhibitors. Compound C has been widely used as an AMPK inhibitor, but it lacks potency and has a poor selectivity profile. The multi-kinase inhibitor, sunitinib, has demonstrated potent nanomolar inhibition of AMPK activity and has scope for modification. Here, we have designed and synthesized several series of oxindoles to determine the structural requirements for AMPK inhibition and to improve selectivity. We identified two potent, novel oxindole-based AMPK inhibitors that were designed to interact with the DFG motif in the ATP-binding site of AMPK, this key feature evades interaction with the common recptor tyrosine kinase targets of sunitinib. Cellular engagement of AMPK by these oxindoles was confirmed by the inhibition of phosphorylation of acetyl-CoA carboxylase (ACC), a known substrate of AMPK, in myeloid leukemia cells. Interestingly, although AMPK is highly expressed and activated in K562 cells these oxindole-based AMPK inhibitors did not impact cell viability or result in significant cytotoxicity. Our studies serve as a platform for the further development of oxindole-based AMPK inhibitors with therapeutic potential.

A high-purity malic acid lin's preparation method

-

Paragraph 0042; 0043, (2019/04/04)

The invention relates to a high-purity malic acid lin's preparation method, the method comprises the following steps: (1) the formula II compound as a starting material, the use of 1 - ethyl - (3 - dimethyl amino propyl) carbonylamino-carbodiimide hydrochloride with 1 - hydroxy benzotriazole as the condensing agent, under certain temperature and N, N diethylethylenediamine reaction to obtain compound III; (2) in the step (1) the reaction solution, between the step (1) the resulting reactant with 5 - fluoro indole - 2 - one reaction at certain temperature, to obtain compound IV; (3) in the step (2) of the reaction solution, so that the step (1) the resulting reactant with L - malic acid reaction at certain temperature, to obtain compound I; providing at least to a certain extent one of the solve the above technical problems or at least provide a useful commercial choice. The reaction route is operating time is short, simple operation, reaction system is stable, higher product yield, purity of the product is relatively high, it is suitable for industrial production.

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